Guesthouse vacation rentals in Windsor and Maidenhead

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Top-rated guesthouse rentals in Windsor and Maidenhead

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

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Guest favorite
An open-plan kitchen and living area features a wooden countertop with bar seating. The room is illuminated by natural light from the skylight, highlighting the contrasting blue and white walls. A cozy sofa and decorative artwork create a welcoming space.
Guesthouse in Berkshire
4.95 out of 5 average rating, 155 reviews

Windsor Home with Free Parking

Welcome to our 1-bedroom, skylit, guest house with off-road parking & private patio. Located in a quiet cul-de-sac close to Legoland, Windsor Racecourse, and Windsor Castle, our home is the perfect retreat after a long day of sightseeing. The bedroom can be set up with either a kingsize bed or 2 singles on request, while the sofa bed can comfortably fit 2 people. Our family run Airbnb is a great fit for families with kids, a couple or a small group of friends. Any questions, please just ask!

Guest favorite
The open-plan living area features a contemporary kitchen with sleek cabinetry and modern appliances. A glass coffee table sits atop a colorful area rug in front of a cozy sofa. Natural light fills the space through two windows, accented by a vase of fresh tulips.
Guesthouse in Datchet
4.92 out of 5 average rating, 516 reviews

Luxury ♥️ 1 bed apartment Windsor Legoland Heathrow

Private self contained bungalow situated close to Windsor town centre. One-bedroom boutique style property plus a double pullout sofa bed, equipped with fully-fitted kitchen , lounge and bathroom with washing machine. Ideal for families visiting Legoland or historic Windsor, with excellent transport links, travel to central London takes just under an hour from Datchet station. Luxury features including a 'rain' shower, 400 thread count Egyptian cotton bedsheets Dolce gusto coffee machine

Top guest favorite
The exterior of the Brickmaker’s Loft displays a charming white facade with brown accents and multiple arched windows. A spiral staircase leads to the entrance, and a well-maintained garden is visible, featuring lush green grass and flower beds along the edge.
Guesthouse in Binfield
4.98 out of 5 average rating, 185 reviews

The Brickmaker’s Loft

A newly fitted one bedroom apartment, with living area, full kitchen, large bedroom with king size bed, a full size single bed in the eaves, and an extra single bed if needed. We’ve kitted the Brickmaker’s Loft out with everything you would need. The kitchen has an oven, fridge, dishwasher, kettle, toaster, microwave and all the normal cooking bits, crockery etc. The bathroom has a walk-in shower, loo, and sink, and a washing machine if you need it. The bedroom is a lovely relaxing space.

Guest favorite
The exterior of the lodge is showcased at night, highlighting warm lighting that illuminates the brick and wood paneling. Window shutters are closed, and a pathway leads to the entrance, accompanied by foliage and outdoor elements.
Guesthouse in Bracknell Forest
4.97 out of 5 average rating, 233 reviews

Garden Lodge – Private Guest Suite in Bracknell

Detached guest lodge next to our family home in Bracknell. Lovely quiet location, just 0.7 miles from central Bracknell (The Lexicon). A modern bedroom with an ensuite shower room and a light refreshment area. Guests are welcome to enjoy full access to our family garden. 3 mins walk to Little Waitrose supermarket (open 24h), or KFC 5 mins walk to Harvester pub 7 mins walk to Leisure Centre (swimming pool, gym, spa, racket sports) 15 mins walk/5 mins drive to train station/central Bracknell

Guest favorite
A modern kitchen features light grey cabinetry with a farmhouse sink and stainless-steel appliances. A decorative backsplash with blue and beige tiles adds color. A small table and seating area are situated nearby, creating a functional and inviting cooking space.
Guesthouse in Pirbright
4.9 out of 5 average rating, 125 reviews

Lakehouse in Pirbright,Surrey

A peaceful private annex in a wonderful semi-rural location in the picturesque village of Pirbright. The annex has off street parking and its own separate entrance. Pirbright is an archetypal Surrey village, with a pretty village green and two excellent pubs. Surrounded by beautiful countryside it is perfect for walking and cycling. Brookwood mainline station is 2 miles away, providing a direct service to Waterloo. Guildford and Woking are close by providing theatres, bars and restaurants.

Guest favorite
A charming cottage is framed by a well-tended garden featuring a thatched roof. Comfortable seating is arranged on a grassy area, accompanied by a small table. The entrance door is flanked by windows adorned with flower pots, creating a welcoming look.
Guesthouse in Cookham Dean
4.85 out of 5 average rating, 110 reviews

Charming Cottage, dogs welcome, private garden .

A pretty cottage fully equipped for a comfortable holiday/ stay! Set back from the road, a peaceful haven. Private garden & parking. Easy walk to all local amenities & The River Thames. Great pubs &Michelin Star restaurants locally. The Chiltern Way offers a stunning path to all cyclists & walkers. Gorgeous old Towns of Windsor ( Legoland& Castle) Henley( Regatta & Festival)& Marlow (Tom Kerridge) , Cliveden, The Stanley Spencer Gallery,Train -London Paddington. M4 M40, Bicester Village .

Superhost
A bright studio space features a spacious bed with crisp white linen, set against a backdrop of exposed wooden beams. A comfortable sofa is nearby, and sliding glass doors offer views of the garden, enhancing the feeling of openness and light.
Guesthouse in Cookham
4.89 out of 5 average rating, 556 reviews

Riverside Boathouse

A warm and cosy studio style converted boat house on the edge of the River Thames in Cookham, Berkshire. Separate from the main house, the double glazed studio boathouse with en-suite, decorated beautifully. Egyptian cotton linen and nice towels. Relax with views of the river. Blackout blinds, kitchen, en-suite shower room, fridge, double glazing, heating, TV, WIFI, laptop area, outdoor seating/picnic blanket, umbrellas, off road parking, boat mooring, EV Charging Point (fee applies).

Top guest favorite
A bright lounge area features a comfortable sofa with plaid cushions, alongside a dining table and chairs. Large skylights and glass doors illuminate the space, opening to a patio garden filled with greenery. Two framed artworks enhance the inviting ambiance.
Guesthouse in Surrey
5 out of 5 average rating, 273 reviews

Self Contained Cottage in Thames Ditton Village

Beautiful self contained 1 bedroom cottage in the grounds of one of Thames Ditton’s oldest properties. Superbly located next to the river with pubs, restaurants, coffee shops, and village stores close by. Thames Ditton is a pretty village located close to Hampton Court, Surbiton, and Kingston Upon Thames and 30 minutes by train to London Waterloo. Go Boat hire is a minutes walk and the slipway to the Thames is opposite the house if you have your own paddle board/canoe.

Guest favorite
A light-filled living area features a gray sectional sofa with a patterned throw, a bright yellow bookshelf stocked with books, and a flat-screen TV mounted on the wall. Large windows allow natural light to illuminate the space, complemented by warm wooden flooring.
Guesthouse in Twyford
4.97 out of 5 average rating, 180 reviews

Spacious 2 Bedroom Cabin With Pool Table and Patio

The cabin is a fun and light filled space, perfect for families or couples. It boasts its own private patio, which leads to a secluded secret garden with an outdoor roll top bath! Inside there is a pool table and Sky TV. It is in the garden of a family home, situated half a mile from Twyford station, allowing easy access to Henley-on-Thames and London via the Elizabeth line. The cabin is accessed through a secure, key coded gate around the side of the main house.

Guest favorite
A well-lit bedroom features a spacious bed centered on a patterned area rug. Two bedside tables hold lamps, and a small potted plant adds a touch of greenery. The walls are painted in a neutral tone, complemented by wooden flooring.
Guesthouse in Greater London
4.93 out of 5 average rating, 305 reviews

Modern Studio, Heathrow Prime Location.

Kick back and relax in this calm, stylish space. This is the perfect pit stop before travelling abroad or even the beginning of your staycation! Due to the popularity of our first listing we are proud to announce this newly renovated guest house, packed full of amazing amenities and unbeatable customer service! A stones throw away from all Heathrow Terminals with excellent travel links to Central London, this will be your home away from home.

Guest favorite
A spacious living area features high wooden ceilings and large windows allowing natural light. A comfortable sofa is positioned near a fireplace, with a cozy blanket placed atop. A rustic table and chair provide a workspace, while a soft rug adds warmth to the wooden floor.
Guesthouse in Taplow
4.95 out of 5 average rating, 521 reviews

Luxury Rustic Log Cabin... secluded deck & garden

A rustic cabin in lovely gardens adjacent to the main house. It has its own secluded garden & deck. Secure parking in large gravel drive. Ideal for Guests attending weddings/celebrations at Hedsor or Cliveden House Visiting the Gardens, Tea or Spa Day at Cliveden it’s on our doorstep! 8 miles to Windsor, visit a famous Castle. Beautiful walks by the River Thames, very pretty local villages with quaint country pubs Suitable two guests

Top guest favorite
The exterior of the annex is presented, featuring a wooden facade with a tiled roof. A welcoming entrance with large glass doors is visible, surrounded by well-maintained greenery and a grassy area. Fields and trees can be seen in the background under a clear blue sky.
Guesthouse in Pamber End
4.97 out of 5 average rating, 158 reviews

Quiet self contained annex

Fully functional self contained annex for single occupancy (located in close proximity to family house) but in a quiet location with lovely views across fields and no disturbance from main residence. Secure off road parking with latest kitchen facilities for those that want to cook or a nice local pub/restaurant in walking distance for those that don't. (Unable to offer long term lets or double occupancy)

Popular amenities for Windsor and Maidenhead guesthouse rentals

When is the best time to visit Windsor and Maidenhead?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$19,454 GYDG$21,964 GYDG$24,056 GYDG$24,683 GYDG$26,566 GYDG$30,540 GYDG$30,331 GYDG$30,331 GYDG$28,449 GYDG$23,219 GYDG$23,847 GYDG$24,683 GYD
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Quick stats about guesthouse rentals in Windsor and Maidenhead

  • Total vacation rentals

    Explore 80 vacation rentals in Windsor and Maidenhead

  • Nightly prices starting at

    Windsor and Maidenhead vacation rentals start at G$12,551 GYD per night before taxes and fees

  • Verified guest reviews

    Over 5,120 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    80 of Windsor and Maidenhead vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Windsor and Maidenhead rentals

  • 4.8 Average rating

    Windsor and Maidenhead stays are highly rated by guests—averaging 4.8 out of 5!

  • Nearby attractions

    Windsor and Maidenhead's top spots, include Ascot Racecourse, Virginia Water Lake, and Odeon Maidenhead

Destinations to explore